- A
nitrilium ion is a
nitrile that has been protonated, [RCNH]+, or alkylated, [RCNR′]+.
Nitriles are only
weakly basic and are poor nucleophiles, but...
-
leaving group to form a
nitrilium ion. This is
followed by
solvolysis to an
imidate and then
tautomerization to the amide: This
nitrilium ion has been known...
-
dichlorophosphoryl imine-ester intermediate,
while Mechanism II
involves a
nitrilium ion
intermediate (both
shown in brackets). This
mechanistic variance stems...
-
groups may be
divalent or trivalent,
yielding ions such as
iminium and
nitrilium. A
simple onium ion has a
charge of +1. A
larger ion that has two onium...
-
either a
carbenium ion or
covalent species to the nitrile. The
resulting nitrilium ion is
hydrolyzed to the
desired amide. Primary, secondary, tertiary,...
-
Nitrile ylides also
known as
nitrilium ylides or
nitrilium methylides, are
generally reactive intermediates formally consisting of a
carbanion of an alkyl...
-
groups migrates from
carbon to
nitrogen with loss of
nitrogen to give a
nitrilium intermediate 6, as in the
Beckmann rearrangement.
Attack by
water converts...
-
nucleophilic addition of the
isocyanide 6 with its
terminal carbon atom to
nitrilium ion 7. A
second nucleophilic addition takes place at this intermediate...
-
inhibitor for the
treatment of
certain breast cancers.
Protonated nitriles:
Nitrilium Deprotonated nitriles:
Nitrile anion Cyanocarbon Nitrile ylide IUPAC Gold...
-
protonated before nucleophilic addition of the isocyanide,
affording a
nitrilium ion intermediate. This is
followed by the
addition of a carboxylate, acyl...
